- Ether compound and pharmaceutical application thereof in prevention and treatment of diabetes and metabolic syndrome
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The invention relates to an ether compound and a pharmaceutical application thereof in prevention and treatment of diabetes and metabolic syndrome. Specifically, the invention provides a compound as shown in a formula (I), an isomer, a raceme, a prodrug, a solvate, a deuterated substance or a pharmaceutically acceptable salt thereof, and Ar1, Ar2, X, Y and R are defined in the specification.
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Paragraph 0260-0261; 0487-0486
(2021/07/24)
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- C-H Amination of Arenes with Hydroxylamine
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This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.
- See, Yi Yang,Sanford, Melanie S.
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supporting information
p. 2931 - 2934
(2020/04/09)
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- Cobalt-Nanoparticles Catalyzed Efficient and Selective Hydrogenation of Aromatic Hydrocarbons
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The development of inexpensive and practical catalysts for arene hydrogenations is key for future valorizations of this general feedstock. Here, we report the development of cobalt nanoparticles supported on silica as selective and general catalysts for such reactions. The specific nanoparticles were prepared by assembling cobalt-pyromellitic acid-piperazine coordination polymer on commercial silica and subsequent pyrolysis. Applying the optimal nanocatalyst, industrial bulk, substituted, and functionalized arenes as well as polycyclic aromatic hydrocarbons are selectively hydrogenated to obtain cyclohexane-based compounds under industrially viable and scalable conditions. The applicability of this hydrogenation methodology is presented for the storage of H2 in liquid organic hydrogen carriers.
- Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Alshammari, Ahmad S.,Altamimi, Rashid M.,Kreyenschulte, Carsten,Pohl, Marga-Martina,Lund, Henrik,Jagadeesh, Rajenahally V.,Beller, Matthias
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p. 8581 - 8591
(2019/09/12)
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- Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core
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A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane for catalytic reduction of unactivated aromatic hydrocarbons under mild conditions. This reaction is scalable and proceeds in high selectivity without the formation of 1,2,3,4-tetrahydronaphthol byproducts with toleration of sensitive functionalities such as bromide, chloride, fluoride, ketone, ester, and amide.
- He, Yuan,Tang, Jinghua,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 4159 - 4163
(2018/07/29)
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- Method for preparing 5,6,7,8-tetrahydro-1-naphthylamine from 1,8-dinitronaphthalene as raw materials
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The invention discloses a method for preparing 5,6,7,8-tetrahydro-1-naphthylamine from 1,8-dinitronaphthalene as raw materials. The method comprises the following steps of using 1,8-dinitronaphthaleneas raw materials; using raney nickel as a catalyst; using hydrogen gas as a reducing agent; performing reaction for 4 to 12 hours in an organic solvent under the conditions of the hydrogen gas pressure being 1.5 to 2.5MPa and the temperature being 120 to 180 DEG C; performing filtering and concentration on reaction liquid to obtain 5,6,7,8-tetrahydro-1-naphthylamine. The synthesis method providedby the invention has the advantages that the operation is simple, convenient and safe; the catalytic hydrogenation is a green synthesis method; the product yield is high; three wastes are less.
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Paragraph 0017-0038
(2018/11/04)
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- Superelectrophilic activation of 1-nitronaphthalene in the presence of aluminum chloride. Reactions with benzene and cyclohexane
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1-Nitronaphthalene smoothly reacts with benzene and undergoes selective reduction with cyclohexane in the presence of aluminum chloride to give 2,4,4-triphenyl-3,4-dihydronaphthalen-1(2H)-one oxime and 5,6,7,8-tetrahydro-1-naphthylamine, respectively. The mechanistic aspects of these and related reactions are discussed on the basis of DFT, providing insight into the protonation behavior of 1-nitronaphthalene coordinated to AlCl3.
- Zhu, Zhongwei,Genaev, Alexander M.,Salnikov, George E.,Koltunov, Konstantin Yu.
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supporting information
p. 9129 - 9132
(2019/01/03)
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- Method for using 1,8-diaminonaphthalene as raw material to prepare 5,6,7,8-tetrahydro-1-naphthylamine
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The invention discloses a method for using 1,8-diaminonaphthalene as a raw material to prepare 5,6,7,8-tetrahydro-1-naphthylamine. The method comprises the steps that 1,8-diaminonaphthalene serves asthe raw material, raney nickel serves as a catalyst, hydrogen serves as a catalyst, a reaction is conducted under the condition where the hydrogen pressure is 1.5-2.5 MPa and the temperature is 120-180 DEG C for 2-10 h, and a reaction liquid is filtered and concentrated to prepare 5,6,7,8-tetrahydro-1-naphthylamine. The synthesis method is easy and safe to operate; catalytic hydrogenation is a green synthesis method, the product yield is high, and the three wastes including waste gas, waste water and industrial residue are less generated.
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Paragraph 0017-0038
(2018/10/11)
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- A process for the preparation of the compound naphthylamine of process (by machine translation)
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The present invention provides a process for preparing compound naphthylamine process method, characterized in that the polarity of the naphthylamine compound dissolved in a solvent proton gender, added with an auxiliary agent, said assistant agent amount is the quality of the states naphthalene amine compound 0.05 - 0.25 times, in order to Ni as the catalyst, hydrogenation reaction at room temperature, after the reaction, filtration, concentration to obtain a tetrahydronaphthalene compounds, the naphthylamine compound of the formula I as shown in the structural formula: the tetrahydronaphthalene amine structural formula of the compound is shown as formula (II) is shown. The reaction of this invention is completed at room temperature, greatly reduced the production energy consumption. At the same time, the reaction almost in the neutral condition, system conditions apply to acid, alkali, heat sensitive all substrate, wide range of application. In addition, because the reaction of the hydrogen pressure is atmospheric, the need to use a high-pressure autoclave equipment, thereby reducing the safety factor in the production process, and reduces equipment investment, greatly reduce the production cost, and is suitable for large-scale industrial production. (by machine translation)
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Paragraph 0023; 0024
(2017/08/25)
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- Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions
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A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.
- Liu, Jianzhong,Wu, Kai,Shen, Tao,Liang, Yujie,Zou, Miancheng,Zhu, Yuchao,Li, Xinwei,Li, Xinyao,Jiao, Ning
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supporting information
p. 563 - 567
(2017/01/18)
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- Electrochemical Amination of Less-Activated Alkylated Arenes Using Boron-Doped Diamond Anodes
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The anodic C-H amination of aromatic compounds is a powerful and versatile method for the synthesis of aniline derivatives. By using boron-doped diamond (BDD) anodes, a method initially described by Yoshida et al. for electron-rich arenes was expanded to less-activated aromatic systems e.g., simple alkylated benzene derivatives. Anodes based on sp3 carbon seem to be the key for the electrochemical amination reaction. The corresponding primary anilines are obtained in good yields. Despite the cationic intermediates of the electrolytic reaction tert-butyl moieties are tolerated.
- Herold, Sebastian,M?hle, Sabine,Zirbes, Michael,Richter, Frank,Nefzger, Hartmut,Waldvogel, Siegfried R.
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supporting information
p. 1274 - 1278
(2016/03/19)
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- Selective catalytic hydrogenation of polycyclic aromatic hydrocarbons promoted by ruthenium nanoparticles
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Ru nanoparticles stabilised by PPh3 are efficient catalysts for hydrogenation of polycyclic aromatic hydrocarbons (PAHs) containing 2-4 rings under mild reaction conditions. These compounds were partially hydrogenated with good to excellent selectivities just by optimizing the reaction conditions. The influence of the nature of substituents present in different positions of naphthalene on the selectivity of hydrogenation was also studied. Hydrogenation of products containing substituents at position 1 is slower than that of products containing substituents at position 2. In all cases, hydrogenation takes place mainly on the less substituted ring.
- Bresó-Femenia, Emma,Chaudret, Bruno,Castillón, Sergio
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p. 2741 - 2751
(2015/05/27)
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- Quenched skeletal Ni as the effective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons
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Quenched skeletal Ni is an active and selective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons (PAHs). The molecular structure of PAHs significantly dominate the hydrogenation process and furthermore, the distribution of hydrogenated products.
- Liu, Chengyun,Rong, Zeming,Sun, Zhuohua,Wang, Yong,Du, Wenqiang,Wang, Yue,Lu, Lianhai
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p. 23984 - 23988
(2013/11/19)
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- Reduction of polycyclic aromatic hydrocarbons promoted by cobalt or manganese nanoparticles
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A new methodology for the partial reduction of polycyclic aromatic and heteroaromatic hydrocarbons under mild reaction conditions is presented, the process being a reasonable alternative to the catalytic hydrogenation or the Birch reaction. The reduction protocol described is based on the use of cobalt or manganese nanoparticles generated in situ in a simple and economic way, by reduction of commercially available CoCl2·6H2O or MnCl2·2H2O in the presence of lithium sand and the corresponding PAH, acting itself as an electron carrier. The use of a deuterium-oxide-containing cobalt(II) salt allows the simple preparation of deuterium labeled products. The regiochemistry and degree of reduction in the case of 1-substituted naphthalene derivatives markedly depends on the nature of the metal-NPs used.
- Nador, Fabiana,Moglie, Yanina,Vitale, Cristian,Yus, Miguel,Alonso, Francisco,Radivoy, Gabriel
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experimental part
p. 4318 - 4325
(2010/07/09)
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- Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists
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A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor.
- Lim, Ju-Ok,Jin, Mi-Kyoung,Ryu, HyungChul,Kang, Dong Wook,Lee, Jeewoo,Pearce, Larry V.,Tran, Richard,Toth, Attila,Blumberg, Peter M.
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experimental part
p. 322 - 331
(2009/04/07)
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- N4-Unsubstituted N1-Arylpiperazines as High-Affinity 5-HT1A Receptor Ligands
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In order to explore the structural requirements for high 5-HT1A affinity, a series of aryl-substituted N1-phenylpiperazines were synthesized and evaluated for their ability to displace -8-OH-DPAT from its specific binding sites in rat frontal cortex homogenates.We found 2-methoxy substitution to be favorable, while 4-methoxy substitution was detrimental for 5-HT1A affinity.Substitution with annelated rings at the 2,3-positions was highly favorable for all investigated compounds, with the exception of a pyrrole ring.All other substitutions, except fluoro, in this class of heterobicyclic phenylpiperazines decreased affinity in the order: ortho>para>meta.The loss of affinity in the ortho and para positions is probably due to steric factors: the substituents either cause steric hindrance with the receptor or prevent the compound from adopting the appropriate conformation for binding to the 5-HT1A receptor.Conformational analysis combined with structure-affinity relationships (SAR) indicates that our arylpiperazines may bind at the 5-HT1A receptor in a nearly coplanar conformation.Observed interactions of the compounds in our 5-HT1A receptor model appeared to be in agreement with SAR data.The aromatic part of the arylpiperazine moiety has ?-? interactions with the aromatic residues Trp161 and Phe362 in helices IV and VI, respectively.The positively charged protonated basic nitrogen forms a hydrogen bond with the negative charged Asp116 in helix III.The ammonium-aspartate complex is surrounded by aromatic residues Trp358 and Phe361 in helix VI.A lipophilic pocket is formed by Phe362, Leu366 (both helix VI), and the methyl group of Thr200 (helix V).In agreement with the model, addition of a methyl substituent to the structure of the benzodioxine analogue 12 in this region, yielding 13, is favorable for 5-HT1A receptor affinity.Unfavorable positions for substitution with bulky groups, like the 3- and 4-positions in the benzofuran compound 14, are explained by steric hindrance with the backbone atoms of helix V.Thus, we were able to rationalize the 5-HT1A SAR of existing N1-phenylpiperazines, as well as a series of newly synthesized bicyclic heteroarylpiperazines, in terms of receptor-ligand interactions.Several of these N4-unsubstituted compounds had affinities in the low-nanomolar range.
- Kuipers, Wilma,Wijngaarden, Ineke van,Kruse, Chris G.,Amstel, Marian ter Horst-van,Tulp, Martin Th. M.,IJzerman, Adriaan P.
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p. 1942 - 1954
(2007/10/02)
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- Thermolabile Hydrocarbons, 31. - Stereoselective Formation and Cleavage of the Dimers of the 1-(5,6,7,8-Tetrahydro-1-naphthyl)neopentyl Radical
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The 1,2-diaryl-1,2-di-t-butylethanes meso- and DL-6 are synthesised by partial catalytic hydrogenation of the parent dinaphthylethanes 5.The crystal structure of meso-6 was obtained experimentally and calculated by molecular mechanics methods (MM2).It is shown, that 1-(5,6,7,8-tetrahydro-1-naphthyl)neopentyl radical 8 forms its dimers 6 with high stereoselectivity, e.g.DL-6: meso-6 = 45 (at -20 deg C) and 7.07 (at 100 deg C).The selectivity was measured over a range of 300 K by using several radical precursors.The difference of the enthalpy of activation has been derived for the two dimerisation reactions: ΔH(excit.)dim (DL - meso) = -2.8 +/- 0.2 kcal/mol.The cleavage of DL-6 and meso-6 into 8 was measured kinetically, and the enthalpies of activation ΔH(excit.)dis = 46.2 +/- 0.6 (DL-6) and 52.6 +/- 1.3 kcal/mol (meso-6) and the entropies of activation ΔS(excit.)dis = 8.4 +/- 0.6 (DL-6) and 20.0 +/- 2.5 e.u. (meso-6) have been obtained.A complete thermodynamic cycle is constructed by using the calculated (MM2) heats of formation ΔHf0 = -27.6 (DL-6) and -30.0 kcal/mol (meso-6).Thus, the diastereomer (DL-6), which is formed preferentially, appears to be the thermodynamically and kinetically less stable one.It turns out, that the high stereoselectivity of the dimerisation of 8, compared to the parent 1-phenyl-neopentyl radical (2a), is mainly caused by the steric repulsions between the approaching radicals. Key words: Bond-formation, C-C, stereoselectivity of; bond cleavage, C-C, kinetics of; calculations, force field.
- Peyman, Anuschirwan,Beckhaus, Hans-Dieter,Kramer, Dirk,Peters, Karl,Schnering, Hans Georg von,Ruechardt, Christoph
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p. 1989 - 1996
(2007/10/02)
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